I went through a a similar excercise last year. I had accumulated quite a few bikes that I just liked with no rhyme or reason and a lot of overlap. Then I moved into a 1 bedroom apartment. My daughter started telling people I lived in a bike shop. I decided to keep one example of each of Reynolds nicer tube sets. I guess I should call my Reynolds Collection. I've got bikes built up in Reynolds 531C, 753R and I'm working on my 653 frame now. I have an 853 Schwinn Peloton but I would like to replace it with a LeMond. I have a Specialized AWOL so I'm keeping my eyes open for a early AWOL expert frame made from Reynolds 725. When I find one I'll swap the parts over from mine. I still have a few bikes that don't fit the collection like my aluminum hardtail MTB. I live in a great mountain biking area so i'll keep that. I have one beater all weather grocery getter bike. And I have a Serrota thats made from Columbus SLX. That thing is a keeper so I justify it as the bike I measure the others against.

So far I've gotten rid of a modern gravel grinder and a modern road bike both All City's, an 80's Trek 620, a mid 00's full suspesion MTB, a department store cruiser bike (Columbia) and a Miyata 912

I think you've made good choices on what you're keeping and like the suggestions of a 40's American Track racer, 50's Italian City Bike etc. For the current decade bike I would build a steel framed disc brake Gravel Grinder with clearance for larger tires like an All City Macho Man.

I'm looking forward to following your progress.